After visiting the water slide, 15 tennis courts, par-72 golf course, or luxury spa at the Naples Grande Beach Resort, take a stroll to the Waterside shops. Located only a block from the Naples Grande (& steps from Saint William Catholic Church) this open air upscale mall is home to 60 luxury retailers and restaurants featuring shops such as Gucci, Louis Vuitton, Cartier, Hermes, Apple, Tesla and Saks Fifth Avenue. Have health conscious fare at True Food Kitchen Restaurant or people watch from the outdoor bar while eating Italian Fare at Brio.
If not staying beachfront, access the public beach at 5000 Gulf Shore Blvd N, or at the end of Vanderbilt Beach Road. Through Naples Beach Water Sports you can rent paddle boards, WaveRunners, and take Banana Boat and Parasail rides. Adventurer Reagan loves them all.
The Trolley gives you a "Hop on - Hop off" narrated tour of all of Naples so you can learn about the whole town (100 points of interest). The whole tour takes 2 hours and you can purchase your tickets in advance at a discount through TripAdvisor.
You can fish from the Historic Naples Pier (every day but Sunday) or just take a stroll down it to enjoy the fantastic views. When the waves are high, you can sometimes watch surfers catching a wave in the water nearby. Find the pier at the west end of 12th Avenue South.
We can’t come to Naples without a visit to Tommy Bahama Restaurant and Bar. No one does coconut shrimp or tuna poke like TB, and we love the live tropical music. Wander up and down Third Street South (considered the birthplace of Naples on the National Register of Historic Places) and enjoy the many shops and restaurants. The Tommy Bahama Relax Store is located where there was originally a Seminole Native American trading post.
One of the few places you can see a honey badger, the Naples Zoo allows you to get in very close range of many of the animals. The Naples Botanical Gardens, where you can see unique tropical plants, are worth a trip, too.
At the Mercato, you can wander from The Pub (a traditional British watering hole), to Bar Tulia (with unique drinks and Italian fare), and finish your night at the Cavo Lounge and Blue Martini for local live entertainment and DJs. If you enjoy a good cigar, stop by Rocky Patel’s Burn (rated nationally as one of the best cigar lounges) before heading home.
Take a Double Sunshine cruise of Naples Bay, Port Royal, and the Gulf of Mexico. You are sure to see dolphins and a variety of birds, sometimes catching a glimpse of a manatee or a loggerhead sea turtle.
If you are going to be in the Naples area a little longer than the weekend, take a trip to the Everglades, the United States’ largest subtropical wilderness. You can see alligators, the roseate spoonbill, the American crocodile, and manatee. Cruise across the wetlands on an airboat. And later, stop by the historic Rod and Gun Club for lunch and a game of pool inside the bar, where you can see the newspaper clippings of famous past visitors, from Roosevelt (among five presidents), to John Wayne, to Ernest Hemingway, and Mic Jagger. It's definitely Old Florida and off the grid - so much so that in the past, those on the run for rum-running, drugs, and even murder were known to have hidden here.
If you have time for an extra day-trip, visit Thomas Edison, Henry Ford, and Harvey Firestone’s summer homes in Fort Myers. Ford worked for Edison, and then they became research partners. Disliking the winters in the North, Edison came to the subtropical area and began experimenting with the unusual indigenous plant fibers as filaments for his electric lights. You can see many of their early inventions here, including a Model T that Ford gave Edison.
Visit the shops and restaurants or just wander the pedestrian-friendly street. Usually there is live music and lots to see. Have some chocolate at Kilwins or an ice cream at Regina’s; have a cocktail on the Del Mar balcony and people-watch, or a drink and dance at the bar at Verginas. We enjoy eating at Osteria Tulia, The French, and Bice, among others. Or if you are a car aficionado, you may catch a glimpse of anything from a Bugatti Veyron to a Ferrari Daytona SP3 cruising the street.
If you are in the area for a while, take a 3 1/2 hour ride out of Fort Myers on the Key West Express, a jet-powered catamaran. Tour the sights of Key West, including the southernmost point of the continental U.S., Hemingway’s home (featuring the descendants of his ten-toed cats), and Truman’s little White House.